4-Chloro-2-(propan-2-yl)-1H-indene → 4-(3,5-Dimethylphenyl)-2-isopropylindene

HRID 1071206Notes

Reaction equation

HRID 1071206 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]2.[CH3:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[C:19]([CH3:21])[CH:20]=1>CCOCC.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:14][C:15]1[CH:16]=[C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]3)[CH:18]=[C:19]([CH3:21])[CH:20]=1

Participants

5

Reactant 2

HCID 219183974-Chloro-2-(propan-2-yl)-1H-indeneHCID 178425074HCID 178425074, compound

Product 1

HCID 220230144-(3,5-Dimethylphenyl)-2-isopropylindene

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

4-chloro-2-isopropylindene (10.0 g, 54 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-dimethylphenylmagnesium bromide (54 mmol) as a Et2O solution was added under vigorous stirring and the reaction was stirred overnight at room temperature. After overnight stirring, the reaction was slowly quenched with H2O to neutralize unreacted Grignard. The solution was subsequently treated with 100 mL of 10% HCl(aq), neutralized with saturated sodium bicarbonate aqueous solution. The organic layer was dried with magnesium sulfate and the solvent was removed by rotary evaporation. The remaining residue was loaded onto a silica gel column and eluted with hexane. Yield was 5.5 g (39%).

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. stirringAfter overnight stirring
  3. customthe reaction was slowly quenched with H2O
  4. additionThe solution was subsequently treated with 100 mL of 10% HCl(aq)
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. customthe solvent was removed by rotary evaporation
  7. washeluted with hexane

Sources & evidence

ORD record
ord-677d24a720f4451aa85a5f97698ccda8
Source dataset
uspto-grants-2005_06
Patent number
US06903229B2

Reaction notes

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